Ammonium Chloride → 4-amino-3-methyl-1H-Pyrazole-1-acetonitrile

HRID 577744Notes

Reaction equation

HRID 577744 reaction equation
[CH3:1][C:2]1[C:6]([N+:7]([O-])=O)=[CH:5][N:4]([CH2:10][C:11]#[N:12])[N:3]=1.[NH4+].[Cl-]>CO.O.[Fe]>[NH2:7][C:6]1[C:2]([CH3:1])=[N:3][N:4]([CH2:10][C:11]#[N:12])[CH:5]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 19620685(3-Methyl-4-nitro-1H-pyrazol-1-YL)acetonitrile

Product 1

HCID 866796734-amino-3-methyl-1H-Pyrazole-1-acetonitrileYield 20.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (3-methyl-4-nitro-1H-pyrazol-1-yl)acetonitrile (2.6 g, 15.7 mmol), NH4Cl (3.4 g, 62.7 mmol) and Fe powder (3.5 g, 62.7 mmol) in MeOH (60 mL) and water (12 mL) was stirred at 80° C. for 2 days. The mixture was filtered, concentrated and the residue was purified by flash chromatography (MeOH: CH2Cl2 20:1) to give the title compound (440 mg, 15% yield) as brown oil.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe residue was purified by flash chromatography (MeOH: CH2Cl2 20:1)

Sources & evidence

ORD record
ord-616e9d627a014a508b830f9e3eac7751
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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